55519-22-7

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 46, p. 2494, 2003 DOI: 10.1021/jm020546r

Upstream product

• 384-64-5 3,3,3-trifluoro-2-phenylpropene 
• 100-59-4 phenylmagnesium chloride 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 20445-34-5 ICM-I 40N 
• 130865-83-7 Ethyl α-hydroxy-α-(trifluoromethyl)phenylacetate 
• 220886-33-9 1-Phenyl-1-(trifluormethyl)-ethan-1,2-diol 
• 80866-87-1 α-methoxy-α-trifluoromethyl-phenyl-acetonitrile 
• 20445-36-7 2-hydroxy-2-phenyl-3,3,3-trifluoro-2-propanoic acid methyl ester 
• 13006-19-4 α-(Chlordifluormethyl)-α-(trifluormethyl)-benzylalkohol 
• 93923-55-8 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionitrile 

Downstream Products

• 40916-23-2 phenyl(trifluoromethyl)ketene 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 17257-70-4 (R)-α-hydroxy-α-trifluoromethylphenyl acetic acid 
• 20445-34-5 ICM-I 40N 

Relevant academic research and scientific papers

Solvent-free synthesis of quaternary α-hydroxy α-trifluoromethyl diazenes: The key step of a nucleophilic formylation strategy

An efficient, scalable and operationally simple one-pot, 2-step strategy for the nucleophilic formylation of trifluoromethyl ketones is presented. The key step is an unprecedented diaza-carbonyl-ene reaction of formaldehyde tert-butyl hydrazone and triflu

AZABICYCLIC MUSCARINIC RECEPTOR ANTAGONISTS

The present invention generally relates to muscarinic receptor antagonists, which are useful for treating various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to processes for preparing compounds described herein, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors.

Design, synthesis and evaluation of novel hydroxyamides as orally available anticonvulsants

Themisone, also known as Atrolactamide, was found, in the 1950s, to be a very potent anticonvulsant. It was hypothesized that the -CF3 substitution would maintain the anticonvulsant activity. Anticonvulsant testing of our novel compounds by the

Design, synthesis, and evaluation of analogues of 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide as orally available general anesthetics

We have recently discovered a novel class of compounds that have oral general anesthetic activity, potent anticonvulsant activity, and minimal hemodynamic effects. The 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide (1) demonstrated potent ability to reduce the minimum alveolar concentration (MAC) of isoflurane, with no effects on heart rate or blood pressure at therapeutic concentrations. Analogue 1 also had potent oral anticonvulsant activity against maximal electroshock (MES) and subcutaneous metrazol (scMET) models with a therapeutic index of 10 for MES activity. In this study, we further synthesized nine new racemic analogues and evaluated these compounds for effects on isoflurane MAC reduction and blood pressure. Preliminary data demonstrate potent reduction in the isoflurane MAC for two new compounds. Current mechanistic studies were unrevealing for effects on voltage-gated ion channels as a putative mechanism. Liposomal partitioning studies using 19F NMR reveal that the aromatic region partitions into the core of the lipid. This partitioning correlated with general anesthetic activity of this class of compounds. Further, compound 1 was used at a concentration of 1 mM and slightly enhanced GABAA current in hippocampal neurons at 10 μM. Altogether, 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide exhibited excellent oral general anesthetic activity and appears devoid of significant side effects (i.e., alterations in blood pressure or heart rate).

Catalytic aerobic oxidative decarboxylation of α-trifluoromethyl-α-hydroxy acids to trifluoromethyl ketones

The oxidative decarboxylation of α-trifluoromethyl-α-hydroxy acids to trifluoromethyl ketones is carried out under mild catalytic aerobic conditions using a cobalt(III) complex in the presence of pivalaldehyde.

Enantioselective synthesis of α-hydroxyacids through oxidation of terminal alkenes with AD-mix/TEMPO

α-Hydroxyacids can be enantioselectively prepared by means of a two- step oxidation process, involving first the asymmetric dihydroxylation of a terminal alkene and subsequent oxidation with TEMPO/NaOCl/NaClO2 in good to excellent yields. No fragmentation of the glycol intermediate was detected. (C) 2000 Elsevier Science Ltd.

α-TRIFLUOROMETHYL-α-HYDROXY CARBOXYLIC ACIDS

The methyl esters of α-trifluoromethyl-α-hydroxy carboxylic acids were obtained by the reaction of methyl trifluoropyruvate with organometallic reagents (Cd, Mg, Zn).The characteristic features of the reactions in relation to the nature of the alkylating agent were demonstrated.

A MODIFIED SYNTHESIS OF MOSHER'S ACID AND ITS USE IN A SENSITIVE STEREOISOMER ANALYSIS OF AMINO ACID DERIVATIVES

A convenient and sensitive method for stereoisomer analysis of amino acid derivatives is described.It is based on the (19)F NMR-analysis of mixtures containing epimers of N-.-methoxy-.-trifluoromethyl-phenylacetyl alanine (MTPA).An improved procedure for the synthesis of MTPA is given.